Dimethylamine → HCID 70656206, compound

HRID 872679Notes

Reaction equation

HRID 872679 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([C:7]([NH:9][C@@H:10]([CH3:27])[CH2:11][N:12]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[C:19]([Cl:25])[C:18]=3[CH3:26])=[N:13]2)=[O:8])[N:6]=1.[CH3:28][NH:29][CH3:30].C1COCC1>N1C=CC=CC=1>[Cl:25][C:19]1[C:18]([CH3:26])=[C:17]([C:14]2[CH:15]=[CH:16][N:12]([CH2:11][C@@H:10]([NH:9][C:7]([C:5]3[N:6]=[C:2]([N:29]([CH3:30])[CH3:28])[S:3][CH:4]=3)=[O:8])[CH3:27])[N:13]=2)[CH:22]=[CH:21][C:20]=1[C:23]#[N:24]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 70656369HCID 70656369, compound

Product 1

HCID 70656206HCID 70656206, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

(S)-2-bromo-N-(1-(3-(3-chloro-4-cyano-2-methylphenyl)-1H-pyrazol-1-yl)-propan-2-yl)thiazole-4-carboxamide (0.247 g, 0.531 mmol) was added into a microwave test tube with dry pyridine. The mixture was bubbled with nitrogen and dimethylamine 2 M in THF (1.329 ml, 2.66 mmol) was added. The reaction mixture was heated with microwaves at 120° C. for 10 h. The crude product was evaporated, diluted with DCM, washed with 1M Na2CO3 and water. The product was purified with Flash-chromatography. Yield 63.2%. 1H-NMR (400 MHz; CDCl3): δ 1.25 (d, 3H), 2.53 (s, 3H), 3.00 (s, 6H), 4.32 (dd, 1H), 4.41 (dd, 1H), 4.55 (m, 1H), 6.41 (d, 1H), 7.30 (d, 1H), 7.52 (m, 3H), 7.74 (d, 1H).

Workup

  1. additionwas added
  2. customThe crude product was evaporated
  3. additiondiluted with DCM
  4. washwashed with 1M Na2CO3 and water
  5. customThe product was purified with Flash-chromatography

Sources & evidence

ORD record
ord-ab2e8e0da28549b381a4a6da8597049d
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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